European Journal of Organic Chemistry

Cover image for Vol. 2016 Issue 4

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.065

ISI Journal Citation Reports © Ranking: 2014: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

VIEW

  1. 1 - 60
  1. Full Papers

    1. Homogeneous Catalysis

      Copper Catalyzed Assembly of N-Aryloxazolidinones: Synthesis of Linezolid, Tedizolid, and Rivaroxaban

      William Mahy, Jamie A. Leitch and Christopher G. Frost

      Article first published online: 9 FEB 2016 | DOI: 10.1002/ejoc.201600033

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      A concise methodology for the construction of three oxazolidinone-based pharmaceuticals: Linezolid, Tedizolid, and Rivaroxaban is reported. All three drugs were synthesized from a common synthetic pool of a di-protected simple amino alcohol. These bioactive structures were assembled using a recently reported one pot copper-catalyzed cyclization and arylation procedure.

  2. Microreviews

    1. Sulfines

      Generation, Reactivity and Uses of Sulfines in Organic Synthesis

      Patrick G. McCaw, Naomi M. Buckley, Stuart G. Collins and Anita R. Maguire

      Article first published online: 8 FEB 2016 | DOI: 10.1002/ejoc.201501538

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      This microreview summarises the development of methods of the synthesis of sulfines and their principal reaction pathways; the diverse modern synthetic approaches to these versatile reactive intermediates has advanced significantly their synthetic potential.

  3. Full Papers

    1. 10-Membered Indolyls

      2,2′-Biindolyl Reactions with Aldehydes

      Daniel Koch, Eva Koch, Eric Desarbre, Birgitta Stensland, Per H. Svensson and Jan Bergman

      Article first published online: 8 FEB 2016 | DOI: 10.1002/ejoc.201501561

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      2,2-Biindolyl reacts with aldehydes, such as benzaldehyde, under acidic conditions to afford 10-membered cyclic products. These products readily undergo transannular dehydrogenation reactions.

    2. Suzuki Cross-Coupling

      A Highly Efficient Pd(PPh3)4-Catalyzed Suzuki Cross-Coupling Method for the Preparation of 2-Nitrobi­phenyls from 1-Chloro-2-nitrobenz­enes and Phenylboronic Acids

      Vijayaragavan Elumalai, Alexander H. Sandtorv and Hans-René Bjørsvik

      Article first published online: 8 FEB 2016 | DOI: 10.1002/ejoc.201501487

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      An efficient microwave-assisted and Pd(PPh3)4-catalyzed Suzuki cross-coupling method for the synthesis of 2-nitrobiphenyls from 1-chloro-2-nitrobenzenes and phenylboronic acids is disclosed. The method exhibits excellent selectivity and fast reaction rates, provides high to excellent yields, and tolerates both electron-withdrawing and -donating groups.

    3. Azapyrenes

      Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties

      Egor V. Verbitskiy, Ekaterina M. Cheprakova, Nadezhda I. Makarova, Igor V. Dorogan, Anatoly V. Metelitsa, Vladimir I. Minkin, Pavel A. Slepukhin, Tatyana S. Svalova, Alla V. Ivanova, Alisa N. Kozitsina, Gennady L. Rusinov, Oleg N. Chupakhin and Valery N. Charushin

      Article first published online: 8 FEB 2016 | DOI: 10.1002/ejoc.201501450

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      A convenient route to a new class of diazapyrene systems, bearing the fused pyrimidine ring, is presented along with their optoelectronic properties. The photophysical and electrochemical properties of these thienoazaacenes have been investigated by UV/Vis absorption and photoluminescence spectrophotometry. Cyclic voltammetry, and X-ray crystallography studies have also been performed.

    4. Peptidomimetics

      Disruption of Native β-Turns: Consequence of Folding Competition between Native and Orthanilic Acid Proline-Based Pseudo β-Turn

      Tukaram S. Ingole, Kuruppanthara N. Vijayadas, K. N. Chaitanya, Amol S. Kotmale, Rupesh L. Gawade, R. G. Gonnade, P. R. Rajamohanan and Gangadhar J. Sanjayan

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501558

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      Peptides comprising β-turn-forming elements and a pseudo β-turn (C9 H-bonding) based on an SAnt-Pro (orthanilic acid - proline) motif were designed. Conformations were investigated by single-crystal X-ray crystallography, 2D NMR spectroscopy, and nOe-restrained computational studies, which revealed that the peptides exhibit C14 or C9 folding and the native β-turn (C10 H-bonding) is disrupted.

    5. Drug Discovery

      Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

      Yi-Xian Li, Ren Iwaki, Atsushi Kato, Yue-Mei Jia, George W. J. Fleet, Xuan Zhao, Min Xiao and Chu-Yi Yu

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501453

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      Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure–activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.

    6. Natural Product Synthesis

      A Straightforward Synthesis of 5-Methylaaptamine from Eugenol, Employing a 6π-Electrocyclization Reaction of a 1-Azatriene

      Daniel A. Heredia, Enrique L. Larghi and Teodoro S. Kaufman

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501566

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      5-Methylaaptamine, an analogue of naturally occurring aaptamine, was synthesized from eugenol by using an A[RIGHTWARDS ARROW]AC[RIGHTWARDS ARROW]ACB ring-construction strategy. The synthetic approach involved the preparation of a 2,3-dihydro-1H-quinolin-4-one system through an aza-Michael/sulfonamidation/Friedel–Crafts cyclization sequence. A 6π-electrocyclization reaction was used to obtain the final B ring.

    7. Huprine Synthesis

      Improved Access to Huprine Derivatives Functionalized at Position 9

      Killian Oukoloff, Sovy Chao, Monika Cieslikiewicz-Bouet, Romain Mougeot, Ludovic Jean and Pierre-Yves Renard

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501433

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      We have developed a new synthetic route to huprine derivatives, potent cholinesterase ligands, possessing a functionalized linker at position 9. This approach involves formation of a vinyl triflate, a Suzuki–Miyaura cross coupling and a Friedländer reaction enabling generation of huprines with alcohols, primary amines, cyano, nitro and carboxylic groups at position 9 in 11–62 % yield.

    8. Si-Functionalised Pyridines

      Sequential Synthesis of Organosilicon-Linked 2-Methoxypyridines by Non-Cryogenic ortho-Metallation Using the nBu2TMPMg·Li Reagent and Hydrosilylation

      Łukasz Struk, Jacek G. Sośnicki, Tomasz J. Idzik and Gabriela Maciejewska

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501570

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      Access to 3-functionalised 2-methoxypyridines, including organosilicon-linked derivatives, is made possible by using a novel nBu2TMPMg Li reagent.

    9. Dötz Reaction

      Regioselective Multicomponent Synthesis of 2,4,6-Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes

      Julio López, Fabiola N. de la Cruz, María Inés Flores-Conde, Marcos Flores-Álamo, Francisco Delgado, Joaquín Tamariz and Miguel A. Vázquez

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501211

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      2,4,6-Trisubstituted phenols were prepared by a retro-Diels–Alder reaction from hindered tricyclic alcohols under acidic conditions. The tricyclic alcohols were obtained by the reduction of cyclohexadienones, which in turn were prepared by the reaction of Fischer dienyl carbenes with terminal alkynes. The dienyl carbenes were prepared from alkynyl Fischer carbenes and pentamethylcyclopentadiene.

    10. Enantioselective Synthesis

      Enantioselective Synthesis of Amino­indan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes

      Yu-ki Tahara, Shuhei Obinata, Kyalo Stephen Kanyiva, Takanori Shibata, Attila Mándi, Tohru Taniguchi and Kenji Monde

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501612

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      The enantioselective synthesis of aminoindan carboxylic acid (Aic) derivatives was achieved by Rh-catalyzed intramolecular [2+2+2] cycloaddition of amino-acid-tethered triynes. Recrystallization gave chiral tethered Aic derivatives with excellent enantiomeric excess. Hydrolysis afforded chiral Aic derivatives, and further synthetic transformation gave free Aic and its dimethyl ester.

    11. 6H-Benzo[c]chromen-6-one

      Synthesis of DNA-Intercalating 6H-Benzo[c]chromen-6-one Derivatives through a Strategic Combination of Garratt–Braverman and Minisci Acyloxylation Reactions

      Prabuddha Bhattacharya, Santi M. Mandal and Amit Basak

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501529

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      Synthesis of DNA-intercalating benzochromenones through a combination of Garratt–Braverman and Minisci acyloxylation reactions is described.

    12. Erythrolactones

      Metabolites from the Euryhaline Ciliate Pseudokeronopsis erythrina

      Andrea Anesi, Federico Buonanno, Graziano di Giuseppe, Claudio Ortenzi and Graziano Guella

      Article first published online: 4 FEB 2016 | DOI: 10.1002/ejoc.201501424

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      Three new molecules, erythrolactones A2, B2 and C2, and their respective sulfate esters (A1, B1, C1) were isolated from cell cultures of Pseudokeronopsis erythrina and their structures elucidated by NMR and MS analyses. The release of pigment granule contents by cold-shock and subsequent analyses revealed that only non-sulfonated molecules are stored. A possible biogenetic route is described.

    13. Fluorinated Amines

      Convenient Access to Di- and Tri­fluoroethylamines for Lead Structure Research

      Amrei Deutsch, Christian Wagner, Carl Deutsch and Anja Hoffmann-Röder

      Article first published online: 3 FEB 2016 | DOI: 10.1002/ejoc.201501576

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      In this manuscript a practical and reliable protocol for the synthesis of new functionalized di- and trifluoroethylamine derivatives is described. Upon addition of Grignard reagents or heteroatom nucleophiles to fluoroalkylated N-aryl-substituted N,O-acetals a broad range of substituted α-difluoro- and α-trifluoroethylamines can be accessed for potential medicinal chemistry applications.

  4. Communications

    1. Trifluoromethylthiolation

      Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3 Group

      Pavlo Nikolaienko, Tülay Yildiz and Magnus Rueping

      Article first published online: 1 FEB 2016 | DOI: 10.1002/ejoc.201501623

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      A mild and rapid trifluoromethylthiolation of diaryliodonium salts allows the synthesis of a wide range of trifluoromethyl thioethers.

  5. Full Papers

    1. Total Synthesis

      Enantioselective Modular Total Synthesis of Macrolides Sch725674 and C-4-epi-Sch725674

      Brijesh M. Sharma, Arjun Gontala and Pradeep Kumar

      Article first published online: 1 FEB 2016 | DOI: 10.1002/ejoc.201501531

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      A convergent total synthesis of Sch725674 has been achieved in 15 steps with a 6.6 % overall yield by stitching together five modules using sequential Jacobsen hydrolytic kinetic resolution, Yamaguchi–Hirao alkynylation, and ring-closing metathesis reactions as the key tools. The influence of protecting groups on the ring-closing metathesis (RCM) macrocyclization has also been studied.

    2. Multicomponent Reactions

      (Imidazol-2-yl)methyl-1,3-propanediones: Regioselective C–H Functionalization of the Imidazole Ring by Acylacetylene/Aldehyde Pairs

      Boris A. Trofimov, Ludmila V. Andriyankova, Lina P. Nikitina, Kseniya V. Belyaeva, Anastasiya G. Mal'kina, Irina Yu. Bagryanskaya, Andrei V. Afonin and Igor A. Ushakov

      Article first published online: 1 FEB 2016 | DOI: 10.1002/ejoc.201501617

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      1-Substituted imidazoles, acylacetylenes, and aldehydes undergo a facile and regioselective cascade reaction under metal-free conditions to give (imidazol-2-yl)methyl-1,3-propanediones through C-2–H functionalization. These reactive building blocks and drug precursors, which have previously been inaccessible, are now readily available by the developed reaction.

    3. Heteroacene Synthesis

      Mechanochemical Synthesis, Photophysical Properties, and X-ray Structures of N-Heteroacenes

      Prasit Kumar Sahoo, Chandan Giri, Tuhin Subhra Haldar, Rakesh Puttreddy, Kari Rissanen and Prasenjit Mal

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201600005

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      The mechanochemical syntheses of N-heteroacenes are described. The syntheses are achieved in high yields within 3–4 h under solvent-free conditions at room temperature. X-ray crystal-structure analysis and photophysical studies showed that the compounds have potential for use in materials applications.

    4. Allylation

      Nickel-Catalysed Bis-Allylation of Activated Nucleophiles with Allyl ­Alcohol

      Rémi Blieck, Mohamed Salah Azizi, Alexis Mifleur, Maxime Roger, Clément Persyn, Mathieu Sauthier and Hélène Bonin

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201501556

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      The nickel catalysed allylation of soft nucleophiles with allyl alcohol gives bis-allylated derivatives in high yields. Nickel(0) precursors are accessible from the in-situ reduction of nickel(II) salts

    5. Glycochemistry

      Chitooligosaccharide Synthesis Using an Ionic Tag

      Laura Gillard, Anh-Tuan Tran, François-Didier Boyer and Jean-Marie Beau

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201501476

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      An environmentally improved synthesis of a key chitooligomer for the construction of biologically active chitooligosaccharides is reported based on an ionic-liquid-supported approach.

    6. Asymmetric Synthesis

      Optically Active 4-Substituted 5-Nitropentan-2-ones: Valuable Chiral Building Blocks for the Stereocontrolled Construction of Spiro-Pyrazolone Scaffolds with Five Contiguous Stereogenic Centers

      Jiao Sun, Cuiping Jiang and Zhenghong Zhou

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201501449

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      Optically active 4-substituted 5-nitropentan-2-ones proved valuable chiral building blocks in the stereocontrolled construction of spiro-pyrazolone scaffolds. A range of spiro-pyrazolones were synthesized in good yields with high levels of diastereo- and enantioselectivity through a base-mediated cascade Michael/aldol reaction between 4-substituted 5-nitropentan-2-ones and unsaturated pyrazolones.

    7. Alkaloid Synthesis

      Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring

      Pierre-Antoine Nocquet and Till Opatz

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201501430

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      A rhodium-catalyzed [4 + 3] cycloaddition and a modified Robinson–Schöpf reaction were each independently applied to the synthesis of 6,7-dehydrotropine which was used as a key intermediate in the synthesis of the alkaloid (±)-scopolamine. Both routes were found to provide similar yields.

  6. Communications

    1. Oxidative Umpolung

      You have full text access to this OnlineOpen article
      Synthesis of 1,4-Diketones from β-Oxo Esters and Enol Acetates by ­Cerium-Catalyzed Oxidative Umpo­lung Reaction

      Irina Geibel and Jens Christoffers

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201600057

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      1,4-Diketones were prepared by cerium-catalyzed, oxidative Umpolung reaction of β-oxo esters with enol acetates. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. The precatalyst is the nontoxic and inexpensive CeCl3·7H2O.

  7. Communication

    1. Acyclic Nucleoside Synthesis

      A Chemoenzymatic Route To Prepare Acyclic Nucleoside Analogues

      Martín A. Palazzolo, Mariano J. Nigro, Adolfo M. Iribarren and Elizabeth Sandra Lewkowicz

      Article first published online: 29 JAN 2016 | DOI: 10.1002/ejoc.201501412

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      The first aldolase-biocatalyzed synthesis of acyclic nucleoside monophosphates is reported. The products are obtained through a clean, simple and effective procedure comprising the regioselective N-alkylation of nucleobases, as cheap starting materials, and the use of a commercially available biocatalyst such as rabbit muscle aldolase.

  8. Full Papers

    1. Natural Product Synthesis

      A Convergent Synthesis of Gonytolide C Using an Intramolecular Oxa-Michael Addition

      Freda F. Li, Darcy J. Atkinson, Daniel P. Furkert and Margaret A. Brimble

      Article first published online: 27 JAN 2016 | DOI: 10.1002/ejoc.201501402

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      The convergent total synthesis of gonytolide C is reported. Assembly of the natural product core scaffold relies on a Horner–Wadsworth–Emmons (HWE) olefination followed by an intramolecular oxa-Michael addition. The study enabled further investigation of an asymmetric oxa-Michael cyclisation for gonytolide C synthesis thus validating this approach to 2,2-disubstituted chromanones.

  9. Communications

    1. Oxysulfonylation

      Oxysulfonylation of Alkenes with Sulfonyl Hydrazides under Transition-Metal-Free Conditions

      Congrong Liu, Lianghui Ding, Guang Guo and Weiwei Liu

      Article first published online: 26 JAN 2016 | DOI: 10.1002/ejoc.201501613

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      An unprecedented method to synthesise β-keto sulfones is demonstrated by trifluoroacetic acid promoted oxysulfonylation of alkenes with sulfonyl hydrazides under transition-metal-free conditions.

    2. Cyclopropanation

      Stereoselective Synthesis of (Sulfonimidoyl)cyclopropanes with (R)-PhSO(NTs)CH2Cl and α,β-Unsaturated Weinreb Amides: Tuning the of Selectivity between C–Cl and C–S Bond Cleavage

      Xiao Shen, Qinghe Liu, Wei Zhang and Jinbo Hu

      Article first published online: 26 JAN 2016 | DOI: 10.1002/ejoc.201501611

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      The first (sulfonimidoyl)cyclopropanation of α,β-unsaturated carbonyl compounds with (R)-PhSO(NTs)CH2Cl was achieved to afford optically enriched (sulfonimidoyl)cyclopropanes in good yields with excellent diastereoselectivities. The reaction shows a broad substrate scope. The Weinreb amide group and the counter cation of the base were found to be important for the selective C–Cl bond cleavage of the sulfoximine reagent.

    3. Regioselective Sulfation

      Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid

      Kenji Fukuhara, Naoyuki Shimada, Takashi Nishino, Eisuke Kaji and Kazuishi Makino

      Article first published online: 26 JAN 2016 | DOI: 10.1002/ejoc.201501568

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      Regioselective, tin-free sulfation of a number of unprotected glycopyranosides was achieved by using a 2,2,2-trichloroethyl-protected sulfurylimidazolium salt as the sulfating reagent and phenylboronic acid for masking the hydroxy groups.

    4. Oxidation of Phenols

      Solvent-Dependent Regio- and Stereo­selective Oxidation of [2.2]Para­cyclophane-Derived Phenols

      Roman P. Zhuravsky, Dmitrii Yu. Antonov, Elena V. Sergeeva, Ivan A. Godovikov, Zoya A. Starikova, Anna V. Vologzhanina and Natalia V. Atman

      Article first published online: 25 JAN 2016 | DOI: 10.1002/ejoc.201501565

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      Oxidation of 4-hydroxy[2.2]paracyclophane and its derivatives with Cu(OH)Cl·TMEDA in MeOH leads to ortho-cyclohexadienones of (Rp*,Rp*) relative configuration, whereas in CH2Cl2 regio- and stereoselective oxidative coupling occurs to produce variously substituted 7,7′-bis[2.2]paracyclophan-4,4′(7H,7′H)-diones with (Sp*,Rc*,Rc*,Sp*) and (Rp,Sc,Rc,Sp) relative configurations.

    5. Ionic Liquids

      Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations

      Daniel J. Eyckens, Megan E. Champion, Bronwyn L. Fox, Prusothman Yoganantharajah, Yann Gibert, Tom Welton and Luke C. Henderson

      Article first published online: 25 JAN 2016 | DOI: 10.1002/ejoc.201501614

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      Solvate ionic liquids have been explored for their suitability as reaction media for organic transformations. These ILs are able to undergo typical optimisation procedures, are inexpensive, and easy to handle.

    6. Asymmetric Catalysis

      Tuning the Basicity of a Metal-Templated Brønsted Base to Facilitate the Enantioselective Sulfa-Michael Addition of Aliphatic Thiols to α,β-Unsaturated N-Acylpyrazoles

      Xiaobing Ding, Cheng Tian, Ying Hu, Lei Gong and Eric Meggers

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501494

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      An effective catalyst for the enantioselective sulfa-Michael addition (SMA) of aliphatic thiols to α,β-unsaturated N-acylpyrazoles is developed by increasing the basicity of the iridium-templated Brønsted base in a straightforward fashion by ligand modification.

  10. Full Papers

    1. C–H Amidation

      Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C–H Amidation Reactions

      Trimurtulu Kotipalli, Veerababurao Kavala, Donala Janreddy, Vijayalakshmi Bandi, Chun-Wei Kuo and Ching-Fa Yao

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501552

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      Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C–H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

    2. Diastereoselective Self-Sorting

      Biphenyl Bis(amino alcohol) Oxalamide Gelators: Complex Gelation Involving Coupled Equilibria, Central-to-Axial Chirality Transfer, Dia­stereoisomer Interconversion, and Self-Sorting

      Tomislav Portada, Krešimir Molčanov, Nataša Šijaković Vujičić and Mladen Žinić

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501261

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      Complex gelation behaviour involving coupled equilibria, diastereoselective self-sorting, diastereomer interconversion, and central-to-axial chirality transfer is shown by some chiral biphenyl-bis(amino alcohol) oxalamide gelators.

    3. Concave Reagents

      Enantiopure Chiral Concave 1,10-Phenanthrolines

      Lisa M. Reck, Gebhard Haberhauer and Ulrich Lüning

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501289

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      Axially chiral concave 1,10-phenanthrolines of different sizes were synthesized and separated into the corresponding enantiomers. Determination of the absolute configuration was achieved by comparison of measured and simulated circular dichroism spectra. First investigations of their influence on the selectivity as ligands in the copper(I) catalyzed cyclopropanation were carried out.

    4. Multicomponent Reactions

      Synthesis of Ugi 4-CR and Passerini 3-CR Adducts under Mechanochemical Activation

      Luis A. Polindara-García and Eusebio Juaristi

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501371

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      A mechanochemical activation strategy that uses high-speed ball milling (HSBM) conditions was applied to isocyanide-based multicomponent reactions (IMCRs) to yield both Ugi and Passerini adducts. This method allows for a combinatorial synthesis of various compounds by using green chemistry principles (i.e., solvent-free conditions, high atom economy, absence of toxic byproducts). HSBM = high-speed ball milling, CR = component reaction.

    5. Oligosaccharide Synthesis

      A Blockwise Approach to the Synthesis of (1[RIGHTWARDS ARROW]2)-Linked Oligosac­char­ides Corresponding to Fragments of the Acid-Stable β-Mannan from the Candida albicans Cell Wall

      Alexander A. Karelin, Yury E. Tsvetkov, Ema Paulovičová, Lucia Paulovičová and Nikolay E. Nifantiev

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501464

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      We have prepared four 3-aminopropyl (1[RIGHTWARDS ARROW]2)-oligomannosides representing fragments of the acid-stable β-mannan from the Candida cell wall. Oligosaccharide donor blocks containing up to four mannose units were successfully employed to introduce β-(1[RIGHTWARDS ARROW]2)-oligomannoside sequences into the chain.

  11. Communications

    1. Polysubstituted Pyrroles

      I2-Promoted Condensation/Cyclization of Aryl Methyl Ketones with Anilines for Facile Synthesis of 1,2,4-Triarylpyrroles

      Hui Xu, Fang-Jian Wang, Ming Xin and Ze Zhang

      Article first published online: 22 JAN 2016 | DOI: 10.1002/ejoc.201501477

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      A novel iodine-mediated cascade condensation/cyclization of aryl methyl ketones with anilines has been successfully developed. According to this straightforward strategy, a variety of 1,2,4-triarylpyrroles were synthesized in moderate to good yields from very simple and readily available starting materials.

  12. Full Papers

    1. Peptide Synthesis

      Chemical Synthesis of Monomeric, Dimeric and Tetrameric Forms of the Ectodomain of Influenza Matrix 2 Protein

      Weiguang Zeng, Kylie J. Horrocks, Amabel C. L. Tan and David C. Jackson

      Article first published online: 21 JAN 2016 | DOI: 10.1002/ejoc.201501569

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      A facile chemical synthesis of the disulfide bond linked tetrameric form of the ectodomain of influenza matrix 2 protein has been established. Acidic conditions were used throughout to minimize randomized thiol-exchange reactions. The synthetic strategies can be adapted for the preparation of other dimeric or tetrameric constructs.

    2. Asymmetric Hydrosilylation

      Diastereoselective Hydrosilylation of N-(tert-Butylsulfinyl)imines Catalyzed by Zinc Acetate

      Anna Adamkiewicz and Jacek Mlynarski

      Article first published online: 20 JAN 2016 | DOI: 10.1002/ejoc.201501318

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      An efficient zinc-catalyzed diastereoselective hydrosilylation of N-(tert-butylsulfinyl)imines has been developed to provide the corresponding secondary amines in high yields with excellent diastereoselectivities (up to 98 % de).

    3. Pyrazine-Based Porphyrinoids

      Pyrazinoporphyrins: Expanding a Pyrrolic Building Block in meso-Tetraphenylporphyrin by a Nitrogen Atom

      Michelle L. Head, Gloria Zarate and Christian Brückner

      Article first published online: 20 JAN 2016 | DOI: 10.1002/ejoc.201501436

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      The stepwise modification of meso-tetraphenylporphyrin to affect the formal replacement of a pyrrolic building block by a pyrazine moiety is described. The optical properties of the resulting pyrazinoporphyrins are porphyrin-like.

    4. Axially Chiral Ligands

      Asymmetric Synthesis of Aromatic and Heteroaromatic α-Amino Acids Using a Recyclable Axially Chiral Ligand

      Jia Li, Shengbin Zhou, Jiang Wang, Aki Kawashima, Hiroki Moriwaki, Vadim A. Soloshonok and Hong Liu

      Article first published online: 20 JAN 2016 | DOI: 10.1002/ejoc.201501442

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      This work introduces a new chiral nucleophilic glycine equivalent containing a recyclable axially chiral ligand. This glycine reagent undergoes alkylation with various benzylic bromides to give aromatic and heteroaromatic α-amino acids of high pharmaceutical potential. The alkylation products were typically isolated in >80 % yield with excellent diastereoselectivity (up to 99:1).

    5. Molecular Devices

      Synthesis and Characterization of Constitutionally Isomeric Oriented Calix[6]arene-Based Rotaxanes

      Valeria Zanichelli, Giulio Ragazzon, Arturo Arduini, Alberto Credi, Paola Franchi, Guido Orlandini, Margherita Venturi, Marco Lucarini, Andrea Secchi and Serena Silvi

      Article first published online: 20 JAN 2016 | DOI: 10.1002/ejoc.201501522

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      Oriented rotaxanes based on a calix[6]arene wheel and nonsymmetric bipyridinium axles have been synthesized. The selective formation of orientational isomers was achieved. Spectroelectrochemistry and electron spin resonance measurements were used to investigate the relative direction of motion of the components.

  13. Microreviews

    1. Carbon Nanostructures

      Organic Functionalized Carbon Nanostructures for Functional Polymer-Based Nanocomposites

      Teresa Gatti, Nicola Vicentini, Miriam Mba and Enzo Menna

      Article first published online: 20 JAN 2016 | DOI: 10.1002/ejoc.201501411

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      Polymer composite materials based on nanosized fillers can be designed to perform specific and complex functions by controlling the physical and chemical interactions between the phases. Strategies for the organic functionalization of carbon nanostructures to improve their dispersion within polymer matrices and enhance the properties of the resulting nanocomposites are presented.

  14. Full Papers

    1. Homogeneous Catalysis

      Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives

      Khac Minh Huy Nguyen and Martine Largeron

      Article first published online: 19 JAN 2016 | DOI: 10.1002/ejoc.201501520

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      Atom-economical! Factors influencing the success of the biomimetic cooperative action of CuBr2 as electron-transfer mediator and a topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary aliphatic amines with o-aminoanilines are disclosed in order to provide a flexible route to benzimidazole derivatives under green conditions.

  15. Communications

    1. N Ligands

      Conjugated, trans-Spanning Ligands as Models for Multivalent p-Phenyleneethynylenes

      Herh G. Vang, Zakarias L. Driscoll, Emily R. Robinson, Casey E. Green, Eric Bosch and Nathan P. Bowling

      Article first published online: 19 JAN 2016 | DOI: 10.1002/ejoc.201501528

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      Conjugated ligands: A trans-spanning ligand that binds AgI and PdII has been developed and studied by X-ray crystallography and 1H NMR spectroscopy. UV/Vis spectroscopy was used to investigate what effect metal binding might have on the conjugation in the para-phenyleneethynylene backbone.

  16. Full Papers

    1. Modified Neurotensin

      Stereoselective Synthesis of β-(5-Arylthiazolyl) α-Amino Acids and Use in Neurotensin Analogues

      Denisa Hapău, Emmanuelle Rémond, Roberto Fanelli, Mélanie Vivancos, Adeline René, Jérôme Côté, Élie Besserer-Offroy, Jean-Michel Longpré, Jean Martinez, Valentin Zaharia, Philippe Sarret and Florine Cavelier

      Article first published online: 18 JAN 2016 | DOI: 10.1002/ejoc.201501495

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      New β-arylthiazole alanines were synthesized in good chemical yields and with 98 % ee using a diastereoselective alkylation; these alanine derivatives were then used as Tyr11 replacements in the construction of neurotensin (NT)[8–13] analogues. The new NT analogues showed improved plasma stability and selectivity towards NTS1 thus preserving the hypotensive properties of the native peptide.

    2. Cascade Reactions

      Cu/Pd-Catalyzed Cascade Reactions of Cyclic Diaryliodoniums and Alkynes – Access to Fluorenes with Conjugate Enynes/Dienes

      Zhenquan Liu, Bingling Luo, Xiaomin Liu, Yumim Hu, Baojian Wu, Peng Huang and Shijun Wen

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501544

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      The Cu/Pd-catalyzed cascade reactions of cyclic diaryliodoniums and alkynes enable the facile construction of structurally diverse fluorenes with conjugate enynes/dines in one or two steps.

    3. Reductive Sulfidation

      Indium-Catalyzed Reductive Sulfid­ation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides

      Takahiro Miyazaki, Shinsei Kasai, Yohei Ogiwara and Norio Sakai

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501559

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      The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S- and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.

    4. Ammosamide B

      An Efficient Approach to the Total Synthesis of Ammosamide B

      Sheng-Wei Yang, Chun-Meng Wang, Kai-Xiang Tang, Jin-Xin Wang and Li-Ping Sun

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501560

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      A new total synthesis of ammosamide B has been realized by using key pyrroloquinoline skeleton precursor 6 (generated in 80 % yield over three steps). The construction of ammosamide B, achieved in 23 % overall yield, required 12 simple steps from a commercially available starting material. Importantly, intermediate 6 serves as an important precursor to other pyrroloquinoline-based natural products.

    5. Drug Discovery

      One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

      Oualid Talhi, Lidia Brodziak-Jarosz, Jana Panning, Barbora Orlikova, Clemens Zwergel, Tzvetomira Tzanova, Stéphanie Philippot, Diana C. G. A. Pinto, Filipe A. Almeida Paz, Clarissa Gerhäuser, Tobias P. Dick, Claus Jacob, Marc Diederich, Denyse Bagrel, Gilbert Kirsch and Artur M. S. Silva

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501278

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      Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 <3 µM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 µM, whereas normal peripheral blood mononuclear cells were not affected.

    6. Nucleoside Synthesis

      4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

      Daniele Mantione, Olatz Olaizola Aizpuru, Misal Giuseppe Memeo, Bruna Bovio and Paolo Quadrelli

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501406

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      Racemic 4-oxocyclopent-2-en-1-yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases.

    7. Asymmetric Synthesis

      A Modular Approach to the Asymmetric Synthesis of Cytisine

      Felix R. Struth and Christoph Hirschhäuser

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501435

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      The asymmetric synthesis of (+)- and (–)-cytisine was achieved by modular application of Matteson homologations to construct the critical asymmetric moiety which is incorporated into a versatile late stage precursor (4a). Intermediate 4a was converted into cytisine in five steps.

  17. Microreviews

    1. Benzylic Fluorination

      Mono- and Difluorination of Benz­ylic Carbon Atoms

      Ana Koperniku, Hongqiang Liu and Paul B. Hurley

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501329

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      A summary of procedures for mono- and difluorination of benzylic carbon atoms is presented. Base-mediated, transition-metal-catalyzed and radical-initiated reactions for the monofluorination of benzylic carbon atoms are described, whereas procedures for their difluorination include base-mediated and radical-initiated reactions.

  18. Full Papers

    1. Natural Product Synthesis

      Synthesis and Configurations of (–)-Furospongin-1 and (+)-Dihydrofuro­spongin-2

      Dong-Xing Tan, Ze-Jun Xu, Hui-Jun Chen, Yikang Wu and Jun You

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501489

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      Despite repeated revisions over the years, the C-13 absolute configuration of both furospongin-1 and dihydrospongin-2 remains questionable, as critical comparisons of optical rotations were made using data recorded in very different solvents. These doubts are now cleared using synthetic samples obtained by a chiral-pool-based route. The configuration of furospongin-1 at C-11 is also fully secured.

    2. Bridging Chiral Calix[4]arenes

      Bridging Chiral Calix[4]arenes: Description, Optical Resolution, and Absolute Configuration Determination

      Feng-Jing An, Wen-Qiang Xu, Shuang Zheng, Shi-Kun Ma, Shao-Yong Li, Run-Ling Wang and Jun-Min Liu

      Article first published online: 15 JAN 2016 | DOI: 10.1002/ejoc.201501467

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      Bridging chiral calix[4]arenes (–)-4a and (+)-4b are a pair of new chiral calix[4]arene enantiomers that have point chirality on their substituted bridging methylene. Their optical resolution is easily achieved with chiral auxiliary (S)-Binol. The absolute configurations of the enantiomers were determined by X-ray crystallographic analysis.

    3. Enantioselective Reduction

      Enantioselective Reduction of Ethyl 3-Oxo-5-phenylpentanoate with Whole-Cell Biocatalysts

      Anna Zadlo, Joerg H. Schrittwieser, Dominik Koszelewski, Wolfgang Kroutil and Ryszard Ostaszewski

      Article first published online: 12 JAN 2016 | DOI: 10.1002/ejoc.201501460

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      Both enantiomers of ethyl 3-hydroxy-5-phenylpentanoate were obtained with excellent optical purities and in high yields by using a whole-cell biocatalyst system.

    4. Proteasome Inhibitors

      Incorporation of the Constrained Peptidomimetic, 5-Methylpyridin-2-one into Peptide Vinyl Sulfones and Peptide Epoxy Ketones is Detrimental for Proteasome Inhibition

      Bo-Tao Xin, Gerjan de Bruin, Jan-Willem Plomp, Bogdan I. Florea, Gijsbert A. van der Marel and Herman S. Overkleeft

      Article first published online: 12 JAN 2016 | DOI: 10.1002/ejoc.201501401

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      Proteasome inhibitors have reached the clinic for the treatment of multiple myeloma and mantle cell lymphoma. Most proteasome inhibitors are based on an oligopeptide scaffold. With the aim to establish whether peptidomimetics are feasible elements in the development of potentially physiologically more tractable inhibitors we studied the use of 5-methylpyridin-2-one as a peptide isoster in peptide vinyl sulfones and peptide epoxy ketones.

    5. Fragrances

      Synthesis and Olfactory Properties of Silicon-Containing Analogs of Rosamusk, Romandolide, and Applelide: Insights into the Structural Parameters of Linear Alicyclic Musks

      Junhui Liu, Yue Zou, Wu Fan, Jian Mao, Guobi Chai, Peng Li, Zhan Qu, Yongli Zong, Jianxun Zhang and Philip Kraft

      Article first published online: 5 JAN 2016 | DOI: 10.1002/ejoc.201501338

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      Sila-Rosamusk, sila-Romandolide, sila-Applelide, and their dehydro derivatives were synthesized from sila-analogs of Artemone and Herbac by hydride reduction and subsequent esterification. The olfactory properties of these compounds allowed a refined musk olfactophore model to be developed. The model shows that it is likely that linear and macrocyclic musks address the same odorant receptors.

  19. Microreviews

    1. Versatile Molecules

      Fifty Years of π-Conjugated Triaz­enes

      Siddappa Patil and Alejandro Bugarin

      Article first published online: 3 DEC 2015 | DOI: 10.1002/ejoc.201501218

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      This microreview highlights progress in synthetically manipulating π-conjugated triazenes in order to increase their reactivity and pinpoint potential applications towards different organic transformations and other research areas.

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